About a year ago, my travels took me to one of the most celebrated tourist destinations in the United States – Florida’s Key West. It’s a city rich in culture, legend, and history; but since the occasion of my visit was my brother’s bachelor party, the vast majority of my sightseeing was relegated to the island’s many bars. I can’t say I had any complaints.
But Key West is much more than just a cluster of bars. And so I promised myself that if I ever returned, I’d take the time to explore the nation’s southernmost city and get better acquainted with its unique character. This past fall, I did exactly that. With a little more time and a lot less urgency, and accompanied not by 13 other dudes bent on drunken shenanigans but by a small, dedicated team of fellow barhoppers, I was able to immerse myself in all those activities that make Key West famous.

Like getting up close to schools of radiantly colored fish on a snorkeling expedition.

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Visiting the onetime home of Ernest Hemingway, a writer whose work earned him a permanent spot in the canon of American literature and whose exploits infuse island lore to this day.

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Relaxing with a cigar on a warm, lazy afternoon.

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Partaking in a sunset celebration in Mallory Square, with musicians and other street performers putting on a show while the sun gracefully bowed out for the day.

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Visiting the concrete buoy marking the nation’s southernmost point and the mile markers designating the start/end point of U.S. Route 1.

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Having an obligatory margarita at the original Margaritaville.

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You could even say we made a few friends this time around.

When not hunting down rogue Jedi and Rebel scum, the Dark Lord of the Sith enjoys relaxing with the banjo.

Now don’t worry – we still did our share of drinking. We chugged down Pirate’s Punch at Captain Tony’s, walking away a few commemorative cups the richer.

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We drank craft rum drinks at the Rum Bar at the Speakeasy Inn, listening to tales spun by bartender Bahama Bob.

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And there was plenty of cheap, light-bodied beer to help us keep the good times afloat.

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All of that might embody the typical weekend in Key West, but we also managed to find a few bars that stood in sharp contrast to traditional island drinking culture.

The Porch

You don’t see many people walking around Duval Street sipping a Guinness. No offense to the godfather of dark beers, but Key West’s perpetually temperate climate naturally calls for lighter fare – Corona, Land Shark, Bud Light, that sort of thing. Even the choosiest beer snobs tend to adopt a when-in-Rome attitude in the Keys. And that’s what makes a Key West craft beer bar so unusual.

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The Porch occupies one half of the Porter Mansion, one of the oldest houses in Key West. Built in 1839, the mansion is named for Dr. Joseph Yates Porter, Florida’s first public health officer, who lived in the house for eight decades. Despite his death in 1927, some say Porter never actually left – the house is reported to be haunted.

But The Porch feels more homey than haunted, with two small, cozy rooms, hardwood floors, and a well-worn, scraped-up bar.

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Movie posters and other memorabilia adorn the walls, giving the space the atmosphere of a man-cave. But for all its interior charm, the best place in The Porch to drink is, well, the porch.

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This spacious veranda, decked out with tables, chairs, and ceiling fans, overlooks the mansion’s garden, with tall, leafy trees helping to keep the sun at bay.

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All you need to complete the picture is a good brew, and The Porch offers 18 rotating beers on draft and another 50 or so in bottles. Everglades Pale Ale is one of a handful of local options. Bold but drinkable, with clear notes of citrus, it’s well suited to sipping on a warm afternoon.

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High-quality craft cider has also made its way to the Keys. Rekorderlig Pear Cider is light, crisp, and sweet, with a natural, subtle pear flavor.

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If beer and cider aren’t your thing, the B. Nektar Meadjito is an unusual mead that features elements of a mojito. It still has a strong honey profile but the sweetness is tempered by hints of mint and lime.

The Porch isn’t the only bar to have set up shop in this allegedly haunted mansion. On the other side of the hall is a bar called, appropriately, The Other Side. And like The Porch, it offers something that’s a bit of a rarity in Key West – classic cocktails.

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Just as complex microbrews tend to take a backseat to lighter, simpler beers in Key West, you don’t see Manhattans or Old Fashioneds on many drink menus down here. Tiki drinks and rum drinks are norm, and they come in every flavor and variety – from hand-crafted cocktails made by a skilled mixologist to slushy plastic cups full of cheap booze poured out of a machine.

But The Other Side caters to drinkers with a more refined palate, or at least anyone looking for a change of pace from the sweeter drinks that dominate the island. It also differs notably in terms of décor; a marble bar, cushy bar seats, and a fireplace give The Other Side a sense of sophistication that sets it apart from the many dives that populate nearby Duval Street.

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Comfortable leather couches, a coffee table, and bookshelf wallpaper make you feel like you’re enjoying a cocktail in a friend’s living room.

Not that it lacks that vital sense of Key West irreverence.

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As with The Porch, I didn’t encounter any ghosts in The Other Side, but I did see plenty of spirits (har har har). The Other Side’s cocktail menu is loaded with classic choices like Manhattans, Blood and Sand, and Negronis, along with some inventive twists like the Raspberry Ramos.

Needless to say, there’s a Hemingway Daiquiri available, made with the excellent Papa’s Pilar blonde rum, grapefruit, lime, sugar, and maraschino liqueur, garnished with a generous wedge of grapefruit. This one was a tad sweeter than other Hemingway Daiquiris I’ve had, but I’m sure “Papa” would still be OK with it.

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The French 75 is pleasantly dry and effervescent, combining gin, lemon, sugar, and Prosecco.

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The unusually named Polish Apple Juice is a variation of the Dalmatian cocktail. Simple and sweet, made with Bison Grass vodka and a rich apple juice, it was like drinking a glass of apple pie.

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And our bartender was happy to whip up something that wasn’t on the menu. The Million Dollar Sunrise is a variation of a Tequila Sunrise.

Rum is unquestionably the most popular spirit in Key West, but tequila might take home the silver. This is, after all, “Margaritaville.” And who knows how much tequila gets consumed via shot glass in Duval Street bars while cover bands tear through classic rock and 80s tunes.

You can get sugary margaritas and shots of Jose Cuervo anywhere in Key West, but Agave 308 is the island’s only bona fide tequila bar.

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Named for its address on Front Street, Agave 308 specializes in tequila-based craft cocktails made with fresh ingredients. There’s more than 50 types of tequila, a small selection of mezcal, and not one bottle of sour mix.

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Despite being steps from popular destinations like Mallory Square and a block from Duval Street, Agave 308 has a tucked-away, hidden feel to it. Dimly lit, with candles on tables and funky artwork on the walls, it can serve as a respite from the hustle and bustle of those arduous Key West days.

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You can, of course, get a margarita here, which by virtue of its being made with fresh lime juice and high-quality tequila will differentiate it from what you might find elsewhere. But bar manager Jules Mavromatis’s drink list is fun and inventive and bears some exploring.

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The Basil Citrus Splash seems to be the most popular offering, and it’s easy to see why. Made with Milagro Reposado tequila, orange, agave, and fresh lime. The distinctive herbal aroma of a basil leaf accompanies every sip.

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The Mezcalita swaps tequila for mezcal and adds jalapeno for a smoky, spicy twist on a margarita. It’s garnished with grilled pineapple, and bits of chopped cilantro contribute an aromatic freshness.

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There’s also a variety of house-infused tequilas, with flavors like ranging from strawberry to pineapple to jalapeno.

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I mean, if you’re going to do a shot of tequila, you might as well make it a good one.

On the final night of my trip, before heading out for the evening, my brother and I were sitting in the hotel bar, quietly sipping drinks and waiting for everyone else to get their shit together. At one point we toasted and made a solemn pledge that we would someday return to this quirky tropical paradise. Key West may seem like party central and all that, but having vacationed there twice now with my brother, it’s become a place where we’ve not only drank and laughed but bonded and made a lot of memories (even if some of them are a little hazy).

And one of the great things about Key West is that when you go back, whether it’s a year later or five years, or ten, so much of it looks exactly the way you remember it. Every day will end with a breathtaking sunset.

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Sloppy Joe’s Bar will be in the same place it’s been since 1937. Same with Captain Tony’s Saloon.

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There’ll be icy rum drinks everywhere you look and plentiful cheap beer to cool you down on a hot day.

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With its deep roots and colorful history, much of Key West feels preserved and unalterable. At the same time, the island isn’t impervious to trends. Microbrews, old-school cocktails, and handcrafted drinks will always be exceptions in a city where people like to keep things simple, but Key West is anything but uniform. And I’d like to think when I go back someday, there’ll still be plenty to discover.